I'm starting to like someone.. I don't know if I should pursue it.?

Question

I KNOW THERE ARE A LOT OF WORDS, BUT PLEASE READ EVERYTHING BEFORE REPLYING.
Thank you.

We're both seniors in high school. I met him last year, when we had English together. He tends to rub a lot of people the wrong way (one of my friends has gone so far to say she hates him) but he recognized my intellect (his words, paraphrased) and has always respected me for it. We don't have any classes together this year, but on MSN he extended me an invitation to sit with his group at lunch, which I promptly accepted. I'm also involved in his anime club, which he invited me to late last year. As well, he offered to drive me to an art class we were both going to take… though the class was cancelled, I found his offer incredibly… well, nice. Apparently, he’s trying to be nicer this year, heh.

Lately (as in the past few weeks) we've been talking on MSN. A lot. He’s entrusted some of his most personal and emotional life stories to me during our conversations. At first, I was surprised by the intimate details he trusted me with – upon inquiry, he clearly stated he feels I’m a closer friend than most and one of the few people who isn’t trying to butt into his life.

His depth of experience is amazing (he’s an army brat) so it’s no surprise we share quite a few interests, especially art (his favoured style is graffiti) and music.

Despite all this, I haven’t ventured so far as to hug him. We haven’t done anything outside of school together - neither alone nor with a group. I’m interested in him, but I’m really afraid to test the waters. There are several reasons for this:

I’m great at structuring my thoughts on paper or screen, but I have trouble talking in actual social situations. Because of this, I don’t think I’m of much interest outside MSN, conversation-wise.
He broke up with his girlfriend of two years just a few months ago. They seemed wonderful together – but he seems bitter over the break-up, in part because his girlfriend bounced back by grabbing another guy as quickly as possible. I don’t think this is the best time to pull anything. Also, she was gorgeous. I’m not unattractive, per se, but I’m not exactly stimulating eye candy.
I don’t want to mess up our friendship by pursing this. It’s not worth the risk.

Given all this… does anyone have advice? I feel really tangled about the whole situation.

Forgot to mention, one of the reasons I'm afraid of pursing this is he has known and knows some AMAZING people. He could have his pick in a second, if he really wanted, so why would he bother with me?

Answer 1

Why wouldn't he be interested in you? You are sweet, articulate, smart, have a charming way about you, whats not to like! I'm sure he finds you an entertaining person to talk to.
But here is the thing.
Military brats are usually more experienced as to partying and even sex. They have been exposed to a lot more than the average kids, due to their moving around so much.
I would hate to see him take advantage of you. Even though you are so intelligent, you don't sound as sophisticated as he is. He's most likely smooth and knows how to say what he thinks you want to hear.
Also, he isn't well-liked, and sounds like a sort of rebel.
But he's been gentlemanly with you so far, so that is a plus, right?
He might carry scars over the broken romance and take it out on you because he is still hurt and lacks trust in females.
After all the pros and cons, I would proceed, but proceed with great care here. DO NOT give your heart away too soon.

Answer 2

Just remain friends for the time being.
You don't want to be a rebound girl or lose a friend because he doesn't share the same feelings as you do.

Give it more time. He seems to care about you too.
Don't rush anything. It seems like things are going rather well right now.

Good Luck, faith